(i) Field of the Invention
The present invention relates to a new process for the preparation of a hydroxylated secondary or tertiary amine compound starting, respectively, from a primary or secondary amine compound, which does not require the employment of an organic solvent such as alcohols or ketones.
(ii) Description of the Related Art
It is known to prepare hydroxylated secondary or tertiary amine compounds, containing a hydroxyl group .beta. to the amine group, by having a primary or secondary amine compound, respectively, react with an epoxy compound, in an organic solvent medium, generally comprising an alcohol or a ketone.
The compounds thus formed give rise to the disadvantage in that they contain traces of organic solvent from the process, making them ill-suited for use in cosmetics, pharmaceuticals, or in any products where the absence of an organic solvent is a requirement.
French Patent 2,099,030 describes a process for the preparation of a compound N-(hydroxyhydrocarbyl)-N-(alkylaminocarboxylate) by reaction between a 1,2-epoxide of hydrocarbide compound and an N-substituted aminocarboxylic acid, in an aqueous medium, optionally in the presence of an alcohol.
However, in order to obtain acceptable yields, this reaction must be carried out in a reactor under very strong agitation, in a manner which is incompatible with implementation on an industrial scale.
In addition, French Patent 2,099,030 recommends purifying the resulting product of the reaction by treating it with an organic solvent medium brought to reflux. It is understood that such purification method leads to the obtaining of a product which cannot be made free of organic solvent and, besides, the employment of a solvent brought to reflux conditions gives rise to significant risks relating to the safety of persons.
Besides, H. Rutzen in Fette, Seifen, Anstrichmittel, Vol. 84, No. 3, 1982, Hamburg, pages 87-92, "Quaterernierung von terti aren Aminsalzen mit langkettigen Epoxiden" describes a process for the preparation of quaternary ammonium compounds by reaction of a tertiary amine compound with a compound containing an epoxy function, in the presence of a phase transfer catalyst.